Yellow-green anthraquinone dye.



eEsT AVAILABLE COP UNITED STATES PATENT carton.

ROBERT E. SCHMIDT AND KARL THUN, Oh ELBERFELD, GERMANY, AS- SIGNORS TO FARBENFABRIKEN OF ELBERFELD'OOJ, OF NEW YORK,

N. Y., A CORPORATION OENEW YORK.

3 Specification of Letters Patent.

YELLOW-GREEN AnrHnAoumons ms,

resented Feb. -13, 19cc.

Appllcation filed Beptember 8,1906. Serial No. 277.696.

-To (all whom, it may concern:

' Be it known that we, ROBERT E. SCHMIDT,

- of new dyestuffs, which are sulfonic acids of 1 the anthracene series. These substances are obtained by condensing the trioxyanthra uinorae sulfonic acid having'proba mu 9.,

ly the orwith prima aromatic amins. By this process the two ydroxy groups in 1 and 4 position are replaced by arylamino groups. For the pre aration of the new dyestuffs, having probab y the general formula,

.quinone sulfonic acid the condensation is best carried out 111 the presence of a reducing agent,

such as stannous chlorid or the like.

The new dyestufi sulfonic acids strain the shape of their alkalinesalts' dark-green pow ders soluble in hot water with a green color.

They; dye unmordanted and chrome-mordanted wool green shades.

The trioxyanthraquinone sulfonic acid which is to be used for condensation is pre pared by treating 1-4-8-trioxyeinthraquinone with sulfonatin agents and boric acid.

' Example 1: en parts, by weight, of 1-4-8- trioxyanthra uinone are added to a solution of ten parts, i)

6o 7. y weight, of crystallized boric f acid in' two hundred parts of furnin sulfuric" acid, (thirty per cent. of SO It is eated to 130 centigrade until a testpor'tion is soluble in water. :Themass of the JGILGtlOH" is .run

parts f stannous chlorid, .(SnCl,+2H,O,)

sulfonic acid are introduced into one 'llhlfilllfid pali'ts of molten paratoluidin. "It is heated w estinfing to.-100 to 120 centiade under access of the'atmospheric air. on the green color of the mixture does not change any more it is allowed to cool to centi ade. It is mixed with methylic alcohol, t e thus-obtained precipitate is filtered off and washed with methylic' alcohol. The new sulfonic acid is then converted into its sodium salt by treatment with sodium carbonate.

- Instead of paratoluidin other aromatic amins-such as. anilin, meta-xylidin, or the like-may be used.

The dyestufi ofExample' 1 can also be-obtained by treating the 1-4diparatoly1diamidO-8-bxyanthraquinones with sulfonating agents and boric acid.

Example 2: Fifteen parts, by weight, of

into one thousand parts of ice-water, and the I crystals separated outare filtered off. Ten

arts of crystallized boric acid, and ten V p of the above 1-4-8-trioxyanthraqui-.

crystallized boric acid are mixed with two hundredparts, by weight, of fumin sulfuric acid, (twenty per cent. of S0 fter the boric acid is dissolved. and the solution has cooled to 30 centigrade. twenty parts, by weight, 3 of 1-4-diparatolyldiamid.o-8oxyan thraquinone are stirred therein-. Stirrin is continued at 30 to 40 centig'rade until a test portion is soluble in a solution of pyridin in water containingflflrom ten to'twentyper cent; of pyridin 'eipro'duct of the reaction is then run into three thousand parts, b

weight, of water. The thussprecipitated su fomc acid filtered .offand'washedwith'cold 35 4-8-tricxyanthrtiquinone with lill'omitiiig Water. It is converted into its sodium salt color and when the dvestufi's dissolved in .by dissolving in boiling Water and reprecipiacetic acid are treated with a solution of 40 tation with common salt. stnnouschlorid in hydrochloric acid they The new dyestuii having probably the are decom'posedunder the formation of a.

5 formula leuco compound of the 1-4-8-tri0xyanthra- NHC,H, guincne sulfonic acid; and dyeing umnor- I anted and chromc-1nordanted wool grcn 45 shades, substantially as hereinbefore described. 4

2. .The herein-described new dye'stufi of the anthracene series, being'1-4-diparat0lyl- M t i l v t 3'9 containing the sulfonic group in the anthrais a dark-green owder; which'i's soluble in quinon'enucleus, obtainable by condensing is concentrated sul ric acid with a violet-blue with paratuluidin the 1-4-5-trioxyanthraqui-;' color. If the new dyestuffs are dissolved in none sulfonic acidwhich is prepared by trvzitdilute acetic acid and then treated with a suing 1-4-8-trioxyanthmquincnc with siilfcnat- 55 lutionofstannouschloridinhydruchlcricacid, I ing agents and limit acid, which dyestutl' is in 7 they are decomposed underthc formation of the shape of its smlium salt n1 (lurk-green v20 8. leuco com bund of the l-4- 8-triuxyanthrw puwdcr soluble in cmn-i-ntrutmlsulfuric acid quinoncsulonicacidfi1tdytsunmurdantcd with-n \-'iul."et-bluc lm' and when the d \'0, g and chrome-murdantcd woolyolkwish-green stull' dissulvvd in acetic acid istrentctlwith 6c Shades. 'f-,--; 1 1 I snhltion Qf stmmuuschlnrid in hytli'tichlorlc Having now-(lescribedcur lllYt'lllltm and livid itisylc't-mnpnscd under thelcrnm timinf 2 5 in whatinanner the sa e is tu l cpcrfcrnml,1 ya, lo n -what we claim as new,'and dcsil vitqst't'ltltf li y ninpnc ullunicgjmii l, 'and d \{ci| ig"unnmi l L 1. The herein-described,jdyos'tull's .of'tluish-"rvvn,shades, substantiallyas hvrpinlwzthesulfunic grou in? heanth ninpnwnnmum-s in-jhv present-1- nftwn subscril'iing wit- ;cleu s,-obtainablc, 31, It Jthprininq aromatic ainins 1 4-84110 thraquincnv sulfonic acidwhicl spr g ULHllng lnit y stulls are in it dark-green ill-121 green agents and bcric. a the shape-cf thej powdc soluble i l dialnidc-8-oxyanthraquinone sulfonic acid 50" 

